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3-Methyl-2-(tributylstannyl)pyridine → 9-Bromo-2-(3-methylpyridin-2-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene

HRID 1530374
Notes
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Reaction equation

HRID 1530374 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9](I)=[CH:10]3)[C:6]=2[CH:16]=1.[CH3:17][C:18]1[C:19]([Sn](CCCC)(CCCC)CCCC)=[N:20][CH:21]=[CH:22][CH:23]=1>CN(C=O)C.[Cu](I)I>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([C:19]4[C:18]([CH3:17])=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:10]3)[C:6]=2[CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 164270983-Methyl-2-(tributylstannyl)pyridineHCID 5820440710-Bromo-2-iodo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepine

Product 1

HCID 683125639-Bromo-2-(3-methylpyridin-2-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azuleneYield 74%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalyst
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 9-bromo-2-iodo-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (200 mg, 0.512 mmol), 3-methyl-2-tributylstannanylpyridine (235 mg, 0.614 mmol), Pd2(PPh3)2Cl2 (36 mg, 0.051 mmol) and copper iodide (29 mg, 0.153 mmol) in DMF (4 mL) was purged with nitrogen and then heated at 100° C. for 1 h using microwave irradiation. The reaction mixture was diluted with MeOH (30 mL) and then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 0.5M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo and the resulting residue was purified by column chromatography (Si-PCC, gradient 0-5% MeOH in EtOAc) affording the title compound as a white solid (135 mg, 74%). LCMS: RT 3.22 min [M+H]+ 355.9/357.9

Workup

  1. customwas purged with nitrogen
  2. custommicrowave irradiation
  3. additionThe reaction mixture was diluted with MeOH (30 mL)
  4. washwas washed with MeOH
  5. washthe product eluted with 0.5M NH3/MeOH
  6. additionThe product containing fractions
  7. concentrationconcentrated in vacuo
  8. customthe resulting residue was purified by column chromatography (Si-PCC, gradient 0-5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-4790dd6a9cc141ce936982a38725ebd9
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090628B2

Reaction notes

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